2-Amino-benzoic acid-4-(pyridin-4-yl-disulfan-yl)pyridine (1/1).

The title 1:1 co-crystal, C(7)H(7)NO(2)·C(10)H(8)N(2)S(2), features a highly twisted 4-(pyridin-4-yldisulfan-yl)pyridine mol-ecule [dihedral angle between the pyridine rings = 89.06 (10)°]. A small twist is evident in the 2-amino-benzoic acid mol-ecule, with the C-C-C-O torsion angle being -7.7 (3)°. An N-H⋯O hydrogen bond occurs in the 2-amino-benzoic acid mol-ecule. In the crystal, mol-ecules are linked by O-H⋯N and N-H⋯N hydrogen bonds into a supra-molecular chain along the b axis. These are connected into layers by π-π inter-actions occurring between pyridine rings [centroid-centroid distance = 3.8489 (15) Å]. The layers are connected along the a axis by C-H⋯O contacts. The crystal studied was a racemic twin.

Related literature

For related studies on co-crystal formation between carb­oxy­lic acids and pyridyl derivatives, see: Arman & Tiekink (2010 ▶); Wardell & Tiekink (2011 ▶); Arman et al. (2011 ▶).

Experimental

Crystal data

C7H7NO2·C10H8N2S2

M = 357.46

Monoclinic,

a = 8.636 (2) Å

b = 12.728 (3) Å

c = 15.688 (4) Å

β = 103.218 (4)°

V = 1678.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 98 K

0.30 × 0.27 × 0.15 mm

Data collection

Rigaku AFC12/SATURN724 CCD diffractometer

3149 measured reflections

3149 independent reflections

3115 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.03

3149 reflections

227 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: nd

Flack parameter: ?

Rogers parameter: ?

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048483/zs2162sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048483/zs2162Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048483/zs2162Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H7NO2·C10H8N2S2	F(000) = 744
Mr = 357.46	Dx = 1.414 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3807 reflections
a = 8.636 (2) Å	θ = 2.7–40.5°
b = 12.728 (3) Å	µ = 0.33 mm−1
c = 15.688 (4) Å	T = 98 K
β = 103.218 (4)°	Block, colourless
V = 1678.7 (7) Å3	0.30 × 0.27 × 0.15 mm
Z = 4

Rigaku AFC12K/SATURN724 CCD diffractometer	3115 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 27.5°, θmin = 2.7°
ω scans	h = −11→10
3149 measured reflections	k = 0→16
3149 independent reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.047P)2 + 0.5616P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3149 reflections	Δρmax = 0.25 e Å−3
227 parameters	Δρmin = −0.23 e Å−3
6 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	1.03842 (6)	0.51910 (4)	0.54403 (3)	0.02643 (12)
S2	0.84697 (6)	0.53636 (3)	0.44236 (3)	0.02623 (12)
O1	0.4176 (2)	0.28720 (11)	0.58052 (9)	0.0301 (3)
H1o	0.425 (4)	0.2527 (19)	0.6269 (10)	0.045*
O2	0.45445 (19)	0.42702 (12)	0.66806 (9)	0.0311 (3)
N1	0.4410 (2)	0.30644 (14)	0.41463 (11)	0.0323 (4)
H1n	0.428 (3)	0.2877 (17)	0.3594 (5)	0.048*
H2n	0.418 (4)	0.2615 (14)	0.4525 (11)	0.048*
N2	0.9169 (2)	0.27383 (14)	0.73043 (12)	0.0302 (4)
N3	0.9212 (2)	0.33036 (13)	0.21812 (11)	0.0271 (3)
C1	0.4350 (2)	0.41116 (14)	0.43227 (12)	0.0212 (4)
C2	0.4369 (2)	0.45314 (14)	0.51627 (12)	0.0213 (4)
C3	0.4360 (2)	0.56293 (16)	0.52675 (13)	0.0261 (4)
H3	0.4382	0.5912	0.5831	0.031*
C4	0.4322 (3)	0.63068 (16)	0.45784 (15)	0.0291 (4)
H4	0.4322	0.7046	0.4665	0.035*
C5	0.4282 (3)	0.58886 (16)	0.37511 (14)	0.0276 (4)
H5	0.4246	0.6347	0.3269	0.033*
C6	0.4294 (2)	0.48188 (15)	0.36270 (13)	0.0241 (4)
H6	0.4263	0.4551	0.3058	0.029*
C7	0.4379 (2)	0.38954 (15)	0.59532 (12)	0.0240 (4)
C8	1.0466 (3)	0.33503 (17)	0.75021 (13)	0.0309 (4)
H8	1.1159	0.3276	0.8064	0.037*
C9	1.0850 (3)	0.40835 (17)	0.69325 (13)	0.0284 (4)
H9	1.1792	0.4492	0.7096	0.034*
C10	0.9828 (2)	0.42076 (14)	0.61162 (12)	0.0221 (4)
C11	0.8478 (2)	0.35789 (15)	0.58888 (13)	0.0236 (4)
H11	0.7764	0.3636	0.5332	0.028*
C12	0.8218 (2)	0.28615 (15)	0.65130 (13)	0.0269 (4)
H12	0.7298	0.2430	0.6363	0.032*
C13	0.8862 (2)	0.45427 (14)	0.35820 (12)	0.0213 (4)
C14	1.0171 (2)	0.38876 (15)	0.36659 (13)	0.0246 (4)
H14	1.0959	0.3849	0.4198	0.030*
C15	1.0288 (3)	0.32873 (16)	0.29402 (14)	0.0268 (4)
H15	1.1186	0.2841	0.2989	0.032*
C16	0.7979 (3)	0.39530 (17)	0.21060 (13)	0.0293 (4)
H16	0.7221	0.3981	0.1562	0.035*
C17	0.7749 (3)	0.45889 (16)	0.27830 (13)	0.0264 (4)
H17	0.6857	0.5045	0.2705	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.0318 (3)	0.0275 (2)	0.0204 (2)	−0.0070 (2)	0.00692 (19)	−0.00252 (17)
S2	0.0341 (3)	0.02419 (19)	0.0212 (2)	0.00549 (19)	0.00813 (19)	0.00134 (17)
O1	0.0455 (9)	0.0265 (7)	0.0172 (6)	−0.0018 (6)	0.0050 (6)	0.0027 (5)
O2	0.0382 (9)	0.0363 (8)	0.0188 (7)	−0.0070 (7)	0.0064 (6)	−0.0036 (6)
N1	0.0531 (12)	0.0238 (8)	0.0201 (8)	0.0013 (8)	0.0088 (8)	−0.0032 (6)
N2	0.0332 (10)	0.0307 (9)	0.0260 (9)	0.0007 (8)	0.0054 (7)	0.0039 (7)
N3	0.0332 (9)	0.0268 (8)	0.0216 (8)	−0.0033 (7)	0.0066 (7)	−0.0034 (7)
C1	0.0197 (8)	0.0249 (8)	0.0181 (8)	0.0014 (7)	0.0023 (7)	0.0000 (7)
C2	0.0188 (8)	0.0256 (8)	0.0185 (9)	−0.0009 (7)	0.0024 (7)	−0.0031 (7)
C3	0.0270 (9)	0.0290 (9)	0.0223 (9)	−0.0009 (8)	0.0053 (8)	−0.0054 (8)
C4	0.0306 (11)	0.0222 (9)	0.0334 (11)	0.0015 (8)	0.0053 (9)	−0.0014 (8)
C5	0.0282 (10)	0.0287 (9)	0.0253 (10)	0.0008 (8)	0.0050 (8)	0.0060 (8)
C6	0.0240 (10)	0.0291 (9)	0.0181 (9)	0.0001 (7)	0.0025 (8)	−0.0005 (7)
C7	0.0210 (9)	0.0301 (9)	0.0201 (9)	−0.0019 (7)	0.0030 (7)	−0.0010 (7)
C8	0.0307 (10)	0.0391 (11)	0.0207 (10)	0.0028 (9)	0.0011 (8)	0.0023 (8)
C9	0.0249 (9)	0.0349 (10)	0.0244 (10)	−0.0004 (8)	0.0033 (8)	−0.0007 (8)
C10	0.0245 (9)	0.0234 (9)	0.0193 (8)	0.0013 (7)	0.0068 (7)	−0.0030 (7)
C11	0.0233 (9)	0.0259 (8)	0.0209 (9)	0.0013 (7)	0.0035 (7)	−0.0009 (7)
C12	0.0290 (10)	0.0247 (9)	0.0267 (10)	−0.0017 (7)	0.0057 (8)	−0.0008 (7)
C13	0.0270 (10)	0.0199 (8)	0.0190 (9)	−0.0005 (7)	0.0092 (7)	0.0015 (6)
C14	0.0283 (10)	0.0246 (8)	0.0203 (9)	−0.0008 (7)	0.0043 (8)	0.0000 (7)
C15	0.0291 (10)	0.0258 (9)	0.0257 (10)	0.0015 (8)	0.0069 (8)	0.0004 (7)
C16	0.0319 (10)	0.0362 (10)	0.0185 (9)	−0.0031 (8)	0.0031 (8)	0.0025 (8)
C17	0.0276 (10)	0.0319 (9)	0.0202 (9)	0.0027 (8)	0.0068 (8)	0.0047 (7)

S1—C10	1.7762 (19)	C4—H4	0.9500
S1—S2	2.0297 (8)	C5—C6	1.376 (3)
S2—C13	1.7761 (18)	C5—H5	0.9500
O1—C7	1.328 (2)	C6—H6	0.9500
O1—H1o	0.8399 (10)	C8—C9	1.384 (3)
O2—C7	1.215 (2)	C8—H8	0.9500
N1—C1	1.365 (2)	C9—C10	1.388 (3)
N1—H1n	0.8800 (11)	C9—H9	0.9500
N1—H2n	0.8801 (10)	C10—C11	1.391 (3)
N2—C12	1.332 (3)	C11—C12	1.394 (3)
N2—C8	1.341 (3)	C11—H11	0.9500
N3—C16	1.332 (3)	C12—H12	0.9500
N3—C15	1.332 (3)	C13—C14	1.387 (3)
C1—C6	1.407 (3)	C13—C17	1.396 (3)
C1—C2	1.418 (2)	C14—C15	1.394 (3)
C2—C3	1.407 (3)	C14—H14	0.9500
C2—C7	1.479 (2)	C15—H15	0.9500
C3—C4	1.377 (3)	C16—C17	1.385 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.396 (3)	C17—H17	0.9500
C10—S1—S2	105.22 (7)	N2—C8—H8	118.2
C13—S2—S1	105.12 (7)	C9—C8—H8	118.2
C7—O1—H1o	112 (2)	C8—C9—C10	118.5 (2)
C1—N1—H1n	117.5 (15)	C8—C9—H9	120.8
C1—N1—H2n	118.2 (15)	C10—C9—H9	120.8
H1n—N1—H2n	119.4 (18)	C9—C10—C11	119.33 (18)
C12—N2—C8	116.85 (18)	C9—C10—S1	115.41 (15)
C16—N3—C15	117.96 (17)	C11—C10—S1	125.26 (16)
N1—C1—C6	117.63 (17)	C10—C11—C12	117.17 (19)
N1—C1—C2	124.29 (18)	C10—C11—H11	121.4
C6—C1—C2	118.07 (17)	C12—C11—H11	121.4
C3—C2—C1	118.91 (17)	N2—C12—C11	124.59 (19)
C3—C2—C7	116.40 (16)	N2—C12—H12	117.7
C1—C2—C7	124.69 (17)	C11—C12—H12	117.7
C4—C3—C2	121.99 (18)	C14—C13—C17	119.32 (17)
C4—C3—H3	119.0	C14—C13—S2	124.98 (16)
C2—C3—H3	119.0	C17—C13—S2	115.70 (15)
C3—C4—C5	118.82 (18)	C13—C14—C15	117.50 (19)
C3—C4—H4	120.6	C13—C14—H14	121.2
C5—C4—H4	120.6	C15—C14—H14	121.3
C6—C5—C4	120.63 (18)	N3—C15—C14	123.7 (2)
C6—C5—H5	119.7	N3—C15—H15	118.1
C4—C5—H5	119.7	C14—C15—H15	118.1
C5—C6—C1	121.56 (18)	N3—C16—C17	123.1 (2)
C5—C6—H6	119.2	N3—C16—H16	118.4
C1—C6—H6	119.2	C17—C16—H16	118.4
O2—C7—O1	122.14 (18)	C16—C17—C13	118.30 (19)
O2—C7—C2	123.34 (18)	C16—C17—H17	120.8
O1—C7—C2	114.52 (16)	C13—C17—H17	120.8
N2—C8—C9	123.6 (2)
C10—S1—S2—C13	−95.20 (9)	C8—C9—C10—C11	−1.5 (3)
N1—C1—C2—C3	177.7 (2)	C8—C9—C10—S1	178.27 (16)
C6—C1—C2—C3	−1.1 (3)	S2—S1—C10—C9	−169.32 (13)
N1—C1—C2—C7	−3.1 (3)	S2—S1—C10—C11	10.46 (18)
C6—C1—C2—C7	178.12 (18)	C9—C10—C11—C12	1.1 (3)
C1—C2—C3—C4	0.5 (3)	S1—C10—C11—C12	−178.70 (14)
C7—C2—C3—C4	−178.81 (18)	C8—N2—C12—C11	−0.3 (3)
C2—C3—C4—C5	0.3 (3)	C10—C11—C12—N2	−0.1 (3)
C3—C4—C5—C6	−0.5 (3)	S1—S2—C13—C14	3.90 (18)
C4—C5—C6—C1	−0.2 (3)	S1—S2—C13—C17	−175.51 (13)
N1—C1—C6—C5	−177.9 (2)	C17—C13—C14—C15	−1.2 (3)
C2—C1—C6—C5	1.0 (3)	S2—C13—C14—C15	179.40 (15)
C3—C2—C7—O2	−7.8 (3)	C16—N3—C15—C14	1.9 (3)
C1—C2—C7—O2	172.92 (19)	C13—C14—C15—N3	−0.6 (3)
C3—C2—C7—O1	171.55 (19)	C15—N3—C16—C17	−1.5 (3)
C1—C2—C7—O1	−7.7 (3)	N3—C16—C17—C13	−0.2 (3)
C12—N2—C8—C9	−0.2 (3)	C14—C13—C17—C16	1.6 (3)
N2—C8—C9—C10	1.1 (3)	S2—C13—C17—C16	−178.97 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2n···O1	0.88 (2)	2.04 (2)	2.667 (2)	128.(2)
N1—H1n···N2i	0.88 (1)	2.15 (1)	3.027 (3)	173.(2)
O1—H1o···N3ii	0.84 (2)	1.79 (2)	2.621 (2)	173 (3)
C17—H17···O2iii	0.95	2.42	3.251 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2n⋯O1	0.88 (2)	2.04 (2)	2.667 (2)	128 (2)
N1—H1n⋯N2i	0.88 (1)	2.15 (1)	3.027 (3)	173 (2)
O1—H1o⋯N3ii	0.84 (2)	1.79 (2)	2.621 (2)	173 (3)
C17—H17⋯O2iii	0.95	2.42	3.251 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) .